Methyl-2-aminobenzoate

This enzyme [EC 1.14.99.15] catalyzes the reaction of 4-methoxybenzoate with AH2 and dioxygen to produce 4-hydroxybenzoate, formaldehyde. A, and water. The bacterial enzyme consists of a ferredoxin-type protein and an iron-sulfur fiavoprotein (FMN). 4-Ethoxyben-zoate, A-methyl-4-aminobenzoate, and toluate can serve as substrates as well. The fungal enzyme acts best on ver-atrate. 

Methyl-4-aminobenzoic acid 3-Methyl-4-ethoxybenzoic acid quantitative conversion 146, 10... 

Place the following compounds in order of increasing basicity, explaining your chosen sequence (a) aniline, benzylamine, diplienylamine (b) 4-aminobenzaldebyde, 4-bromoaniline, methyl 4-aminobenzoate. 

Hydrolysis with CsOH in ethylene glycol at 150° gave methyl 4-aminobenzoate with LiAlH4, partial loss of the fluorine and the methyl group was observed. m No reaction occurred under the conditions of footnote k. n PhC(=NTs)NMe(CH2)2OH was formed in 70% yield. 

Your mixture may be one of the following (1) 50% benzoic acid, 40% benzoin, 10% 1,4-dibromobenzene (2) 50% fluorene, 40% o-toluic acid, 10% 1,4-dibromobenzene (3) 50% phenanthrene, 40% methyl 4-aminobenzoate, 10% 1,4-dibromobenzene or (4) 50% 4-aminoacetophenone, 40% 1,2,4,5-tetrachlorobenzene, 10% 1,4-dibromobenzene. Other mixtures are given in the Instructor s Manual, along with some suggestions about these mixtures. 

Materials. N,N-Dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP) were stirred over powdered calcium hydride overnight, distilled under reduced pressure, and then stored over 4-A molecular sieves. 4-Aminobenzhydrazide (5) was prepared from methyl 4-aminobenzoate and hydrazine monohydrate according to the reported procedure (6). 4,4 -Thiobisbenzenthiol (6) and isophthalic acid (7) were purified by reciystdlization. Phenyl acrylate and 4-nitrophenyl acetate were prepared by the reactions of acryloyl chloride or acetyl chloride with phenol or 4-nitrophenol in the presence of triethylamine and tetahydrofuran, respectively. TrieAylamine (TEA) and tetahydrofuran (THF) were purified by the usual method. Other reagents and solvents were obtained commercially and used as received. 

Methyl 4-aminobenzoate, in A-00105 4-(Methylamino)benzoic acid, in A-00105 2-(Methylamino)biphenyl, in A-00116... 

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